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Also known as: 4-hexylresorcinol, 136-77-6, 4-hexylbenzene-1,3-diol, 4-hexyl-1,3-benzenediol, 4-n-hexylresorcinol, Antascarin
Molecular Formula
C12H18O2
Molecular Weight
194.27  g/mol
InChI Key
WFJIVOKAWHGMBH-UHFFFAOYSA-N
FDA UNII
R9QTB5E82N

Hexylresorcinol
A substituted dihydroxybenzene used topically as an antiseptic for the treatment of minor skin infections.
1 2D Structure

Hexylresorcinol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-hexylbenzene-1,3-diol
2.1.2 InChI
InChI=1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3
2.1.3 InChI Key
WFJIVOKAWHGMBH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCC1=C(C=C(C=C1)O)O
2.2 Other Identifiers
2.2.1 UNII
R9QTB5E82N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4 Hexylresorcinol

2. 4-hexylresorcinol

2.3.2 Depositor-Supplied Synonyms

1. 4-hexylresorcinol

2. 136-77-6

3. 4-hexylbenzene-1,3-diol

4. 4-hexyl-1,3-benzenediol

5. 4-n-hexylresorcinol

6. Antascarin

7. Ascaricid

8. Ascarinol

9. Oxana

10. P-hexylresorcinol

11. Adrover

12. Caprokol

13. Hidesol

14. Crystoids

15. 1,3-benzenediol, 4-hexyl-

16. Prensol

17. 4-hexylresorcine

18. Sucrets

19. Gelovermin

20. Hexylresorcin

21. 4-hexyl-1,3-dihydroxybenzene

22. Ascaryl

23. 4-(1-hexyl)resorcinol

24. Cystoids Anthelmintic

25. 1,3-dihydroxy-4-hexylbenzene

26. Worm-agen

27. Resorcinol, 4-hexyl-

28. Mycoderm

29. 1,3-dihydroxy-4-n-hexylbenzene

30. Nci-c55787

31. St-37

32. S.t. 37

33. Nsc 1570

34. Mfcd00002284

35. R9qtb5e82n

36. Chembl443605

37. Ins No.586

38. Ins-586

39. Nsc1570

40. 1-(2',4'-dihydroxyphenyl)hexane

41. Ncgc00091208-04

42. Hexylresorzin

43. Dsstox_cid_699

44. Hexylresorcinolum

45. E-586

46. Dsstox_rid_75743

47. Dsstox_gsid_20699

48. Hexylresorcin [german]

49. Everfresh

50. 4-hexyl Resorcinol

51. Cas-136-77-6

52. Ccris 888

53. Hsdb 566

54. St 37

55. Einecs 205-257-4

56. Unii-r9qtb5e82n

57. Brn 2048312

58. Ai3-08055

59. Hexylresorcinol [usp:inn:ban]

60. 4-hexyl-benzenediol

61. Hexylresorcinol (usp)

62. Spectrum_000869

63. 1, 4-hexyl-

64. 4-hexylresorcinol, 8ci

65. Spectrum2_000989

66. Spectrum3_000451

67. Spectrum4_000001

68. Spectrum5_000794

69. 4-hexylresorcinol, 98%

70. Wln: Qr Cq D6

71. Hexylresorcinol, Ban, Usan

72. Schembl29107

73. Bspbio_002122

74. Kbiogr_000341

75. Kbioss_001349

76. 4-06-00-06048 (beilstein Handbook Reference)

77. Mls002152930

78. Divk1c_000094

79. Hexylresorcinol [hsdb]

80. Hexylresorcinol [inci]

81. Spectrum1500330

82. Spbio_001057

83. 4-hexylresorcinol [mi]

84. Hexylresorcinol [mart.]

85. 1-(2,4-dihydroxyphenyl)hexane

86. 4-hexyl-1,3-dihydroxy Benzene

87. 4-hexylresorcinol [fcc]

88. Dtxsid1020699

89. Hexylresorcinol [usp-rs]

90. Hexylresorcinol [who-dd]

91. Bcbcmap01_000093

92. Chebi:93749

93. Hms500e16

94. Kbio1_000094

95. Kbio2_001349

96. Kbio2_003917

97. Kbio2_006485

98. Kbio3_001342

99. Ninds_000094

100. 1, 3-dihydroxy-4-n-hexylbenzene

101. Hms1920d09

102. Hms2091j15

103. Hms3885j08

104. Pharmakon1600-01500330

105. Benzene, 4-hexyl-1,3-dihydroxy-

106. Act05713

107. Bcp31316

108. Hy-b0986

109. Nsc-1570

110. Zinc1576892

111. Tox21_111102

112. Tox21_202263

113. Tox21_300357

114. Bbl023042

115. Bdbm50292636

116. Ccg-40207

117. Hexylresorcinol [ep Impurity]

118. Nsc757056

119. S4571

120. Stl008005

121. Hexylresorcinol [ep Monograph]

122. 4-hexylresorcinol, Analytical Standard

123. Akos005683587

124. Tox21_111102_1

125. Cs-4477

126. Db11254

127. Hexylresorcinol [usp Monograph]

128. Nsc-757056

129. Benzene,1,3-dihydroxy,4-hexyl

130. Idi1_000094

131. Qtl1_000043

132. Smp1_000009

133. Ncgc00091208-01

134. Ncgc00091208-02

135. Ncgc00091208-03

136. Ncgc00091208-05

137. Ncgc00091208-06

138. Ncgc00091208-07

139. Ncgc00091208-09

140. Ncgc00091208-11

141. Ncgc00254302-01

142. Ncgc00259812-01

143. Ac-12698

144. Ac-31726

145. As-40438

146. Nci60_001129

147. Smr000112060

148. Sbi-0051404.p003

149. Ft-0618587

150. H0139

151. D04441

152. Ab00052011_05

153. A807126

154. Q229969

155. Sr-05000002054

156. Q-201203

157. Sr-05000002054-1

158. Brd-k99946902-001-02-6

159. Z1259339944

160. Hexylresorcinol, European Pharmacopoeia (ep) Reference Standard

161. Hexylresorcinol, United States Pharmacopeia (usp) Reference Standard

162. 1-(2',4'-dihydroxyphenyl)hexane;hexylresorcinol;4-hexyl-1,3-benzenediol

163. Hexylresorcinol For System Suitability, Europepharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 194.27 g/mol
Molecular Formula C12H18O2
XLogP33.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass194.130679813 g/mol
Monoisotopic Mass194.130679813 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count14
Formal Charge0
Complexity147
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Anti-Infective Agents, Local; Antinematodal Agents; Antiplatyhelmintic Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


It is commonly employed in 1:1000 soln or glycerite in mouthwashes or pharyngeal antiseptic preparation.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 991


MEDICATION (VET): Rare now, as anthelmintic especially since introduction of dichlorvos and other drugs. Topically it is effective bacteriostatic, bactericidal, virucidal, fungistatic, and fungicidal agent at dilutions greater than 1:1000 (0.1%), although latter is safe topically. In ringworm therapy with Aminoacridinium = Aacrisorcin ...

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 260


MEDICATION (VET): Effective against many viruses when aerosoled at 5 mg/cu m. ... Administer orally in oil to reduce local irritation.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 260


For more Therapeutic Uses (Complete) data for HEXYLRESORCINOL (7 total), please visit the HSDB record page.


4.2 Drug Warning

Hexylresorcinol should not be dispensed in ordinary, hard-gelatin capsules as these quickly become brittle, and may break in mouth causing caustic burns.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1174


Hexylresorcinol, given orally, is ineffective but when given by enema, tedious and unpleasant experience for patients, there is immediate symptomatic relief, although cures are rarely attained.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 864


Care should be taken that pills containing drug are swallowed whole or painful ulceration of oral mucous membrane may result.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1174


4.3 Minimum/Potential Fatal Human Dose

probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz and 1 pint (or 1 lbs) for 70 kg person (150 lb). Somewhat less toxic than resorcinol or phenol.

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-127


4.4 Drug Indication

Hexylresorcinol is predominantly employed as the active ingredient in lotions, sprays, or lozenges indicated as a (a) topical antiseptic to help prevent skin infection in minor cuts, scrapes, or burns, or (b) as an antiseptic and local anesthetic for the relief of a sore throat and its associated pain. In addition, hexylresorcinol is used as an active ingredient in various commercial cosmetic skincare products as an anti-aging cream while other studies have looked into whether or not the compound could be used effectively as an anti-inflammatory agent or even as an anti-cancer therapy.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Hexylresorcinol is a phenol derivative, and in typical therapeutic usage is primarily a local anesthetic for topical use on the mucous membranes of the mouth and throat. The local anesthetic like properties of hexylresorcinol is likely due to its sodium channel blocking effects. The agent also demonstrates mild antiseptic activity as well as an apparent anti-inflammatory, demulcent action.


5.2 MeSH Pharmacological Classification

Anthelmintics

Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)


5.3 ATC Code

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AA - Antiseptics

R02AA12 - Hexylresorcinol


5.4 Absorption, Distribution and Excretion

Absorption

Owing to the poor absorption of hexylresorcinol, systemic exposure and symptoms are unusual.


Route of Elimination

When two men received doses of 1 g of hexylresorcinol, an average of 18% of the dose was recovered in the urine within the first 12 hours - thereafter, the compound was not detected in urine samples.


Volume of Distribution

Readily accessible data regarding the volume of distribution of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area.


Clearance

Readily accessible data regarding the clearance of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area.


Dogs were given single doses of 1 or 3 g 4-hexylresorcinol (equivalent to 100 or 300 mg/kg bw) as crystals in gelatin capsules or as a solution in olive oil, and excretion monitored in urine and feces. After administration of 1 g crystalline compound, 29% of the dose was detected in urine and 67% in feces; when the dose was increased to 3 g, 17% was excreted in urine and 73% in feces. Urinary excretion was rapid, mainly in the first 6 hr, and levels were virtually undetectable 12 hr after the lower dose and 24-36 hr following the higher dose. When 4-hexylresorcinol was administered in olive oil, a dose of 1 g resulted in 17% being excreted in urine and 76% in feces, while 10% was excreted in urine and 80% in feces following a dose of 3 g.

WHO Food Additive Series 35: 4-Hexylresorcinol (136-77-6). Available from, as of July 18, 2005: https://www.inchem.org/documents/jecfa/jecmono/v35je04.htm


When two men received doses of 1 g 4-hexylresorcinol, an average of 18% of the dose was recovered in urine within the first 12 hr; thereafter the compound was not detected in urine samples. Fecal excretion accounted for 64% of the dose.

WHO Food Additive Series 35: 4-Hexylresorcinol (136-77-6). Available from, as of July 18, 2005: https://www.inchem.org/documents/jecfa/jecmono/v35je04.htm


5.5 Metabolism/Metabolites

Regarding the metabolism of hexylresorcinol, it has been reported that excretion of the compound in the urine is largely in the form of an ethereal sulfate conjugate.


Human metabolite of 4-hexylresorcinol is ethereal sulfate. /From table/

Sunshine, I. (ed.). CRC Handbook of Analytical Toxicology. Cleveland: The Chemical Rubber Co., 1969., p. 353


It has been reported that 4-hexylresorcinol is excreted via the urine mainly in the form of an ethereal sulfate conjugate ...

WHO Food Additive Series 35: 4-Hexylresorcinol (136-77-6). Available from, as of July 18, 2005: https://www.inchem.org/documents/jecfa/jecmono/v35je04.htm


5.6 Biological Half-Life

Readily accessible data regarding the half-life of hexylresorcinol is not available. Nevertheless, when hexylresorcinol is employed in its primary indication as a topical antiseptic or an oral anesthetic, it is generally accepted that pharmacokinetic considerations do not arise since the pharmacological action is local to the topically applied or oro-pharyngeal cavity area.


5.7 Mechanism of Action

When acting as an oral anesthetic for relieving sore throats, it is generally believed that hexylresorcinol is possibly capable of blocking voltage-gated neuronal sodium channels, which in turn would inhibit the initiation and conduction of nerve impulses for feeling or transmitting pain signals in the local area to which the hexylresorcinol is applied. As an antiseptic agent, studies have demonstrated that hexylresorcinol is capable of eliciting actions like reducing or inhibiting the generation of bacterial biofilm, interfering with bacterial cell chain formation, reducing bacterial adherence of the pharynx, inhibition of glycolytic enzyme and pH drops, and alteration of cell surface hydrophobicity. Unfortunately, there are either antibiotics that function even more effectively at formally treating bacterial growth or there are also other plant-derived phenolic compounds similar to hexylresorcinol that elicit stronger such mechanisms of action. Nevertheless, it is useful for hexylresorcinol to have both anesthetic and certain antiseptic actions for its use in treating various relatively self-limiting scrapes and sore throats that are treated by the over-the-counter products that feature the compound. Early studies in the 1930s and 1940s suggested that there were more effective medicines over hexylresorcinol that could be employed for their anthelmintic effects. As an anti-inflammatory and anti-aging agent, some studies have shown that it may be possible for hexylresorcinol to inhibit the phosphorylation of the immune response mediator NF-kappaB and also elicit a significant skin lightening effect owing to a strong inhibitory effect on tyrosinase and peroxidase and a stimulatory effect on glutathione and E-cadherin syntheses. It is proposed that hexylresorcinol can bind to tyrosinase directly and inhibits its enzyme activity. Literature data suggests that low glutathione levels relates to the deposition of melanin in the skin of humans and other animals, while high glutathione levels inhibit melanogenesis. And ultimately, it is also reported that glutathione depletion increases tyrosinase activity in human melanoma cells, which makes hexylresorcinol's effects on tyrosinase desirable. Finally, there are ongoing studies that have reported hexylresorcinol's abilities to induce the differentiation of SCC-9 squamous cell cell-line by way of the modulation of the E2F-mediated signaling pathway and suppress the growth of squamous cell carcinoma SCC-9 cells in a dose-dependent manner. Moreover, such studies have also shown that hexylresorcinol is seemingly capable of dose-dependent induction of SCC-9 cell apoptosis as well as the inhibition of transglutaminase-2 enzyme activity which can facilitate chemotherapy resistance.


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07-Jun-2021
24-Apr-2024
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